(2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one

Base Information

• Chemical Name: (2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one
• CAS No.: 1257329-16-0
• Molecular Formula: C₃₀H₃₈O₅
• Molecular Weight: 478.629
• Mol file: 1257329-16-0.mol

Synonyms:(2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one

Chemical Property of (2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one

There total 4 articles about (2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

({[(2S,4R)-2,4-dimethylhex-5-yn-1-yl]oxy}methyl)benzene (960012-15-1) + (R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide (303727-84-6) → (2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one (1257329-16-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201001018

Reference yield:

[2S,4R]-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol (143236-77-5) → (2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one (1257329-16-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / Inert atmosphere

2.1: ammonium cerium (IV) nitrate; water / acetonitrile / 0 °C / Inert atmosphere

3.1: pyridine; Dess-Martin periodane / dichloromethane / Inert atmosphere

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

5.2: 1.08 h / -78 - 0 °C / Inert atmosphere

With pyridine; n-butyllithium; ammonium cerium (IV) nitrate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile; 3.1: Dess-Martin oxidation / 4.1: Shioiri alkynylation / 4.2: Shioiri alkynylation;

DOI:10.1002/ejoc.201100244

Reference yield:

(2S,4R)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-methyl-amide (922523-34-0) → (2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one (1257329-16-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: ammonia borane / tetrahydrofuran / Inert atmosphere

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / Inert atmosphere

3.1: ammonium cerium (IV) nitrate; water / acetonitrile / 0 °C / Inert atmosphere

4.1: pyridine; Dess-Martin periodane / dichloromethane / Inert atmosphere

5.1: n-butyllithium; diisopropylamine / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

6.2: 1.08 h / -78 - 0 °C / Inert atmosphere

With pyridine; n-butyllithium; ammonium cerium (IV) nitrate; ammonia borane; water; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile; 4.1: Dess-Martin oxidation / 5.1: Shioiri alkynylation / 5.2: Shioiri alkynylation;

DOI:10.1002/ejoc.201100244

upstream raw materials:

({[(2S,4R)-2,4-dimethylhex-5-yn-1-yl]oxy}methyl)benzene

(R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide

(2S,4R)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-methyl-amide

[2S,4R]-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol

Downstream raw materials:

methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrakis(tert-butyldimethylsilyloxy)-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate

(R,2Z,4E)-methyl 6-((4S,6S)-6-{(1Z,3R,4S,5S,7S,10R,11S,12S,13S,14Z)-4,10-dihydroxy-12-[(4-methoxybenzyl)oxy]-3,5,7,11,13-pentamethylheptadeca-1,14,16-trien-1-yl}-2,2-dimethyl-1,3-dioxan-4-yl)hepta-2,4-dienoate

methyl (2Z,4E,6R,7S,9S,10Z,12R,13S,14S,16S,19R,20R,21S,22S,23Z)-7,9,13,19-tetrahydroxy-21-(4-methoxybenzyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate

(5S,6S,8S,11R)-5-[(R,Z)-4-iodobut-3-en-2-yl]-11-[(2R,3S,4S,Z)-3-(4-methoxybenzyloxy)-4-methylocta-5,7-dien-2-yl]-2,2,3,3,6,8,13,13,14,14-decamethyl-4,12-dioxa-3,13-disilapentadecane